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The Eastern End of Long Island, New York City’s backyard beach getaway, offers a variety of fun activities for all ages and interests. From Riverhead to Greenport to Montauk, there are the Hamptons, North Fork farms and vineyards, breweries, scenic beaches, and stunning views. From tall ship festivals to music festivals to drag racing events, to the Long Island Aquarium, Splish Splash, and the Parrish Art Museum, there’s something for everyone.

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Discover the Town of Southold on the North Fork

East End Getaway has curated a guide to the towns across the North and South Forks, highlighting some of the best of what to see and do plus what the insiders know. This information will help you map and plan your next getaway to the East End of Long Island. Today, we take you inside the town of Southold

Brief Overview of Southold

The town of Southold is the easternmost town on the North Fork containing the following hamlets: Cutchogue, East Marion, Fishers Island, Laurel, Mattituck, New Suffolk, Orient, Peconic and Southold. This bucolic North Fork town stretches over twenty-five miles west to east from Laurel and out to Orient Point and located just over two hours away or about 100 miles from New York City. 

Southold was founded in 1640 by English settlers and soon became a thriving farming and fishing community. Known for its rich history and heritage, the vast town of Southold is an ideal destination for visiting historic sites, vineyards, adventure, water activities and boutique shopping. 

How to Travel to Southold

There are several convenient ways to travel to Southold. From Manhattan, the most direct and fastest route is by train from Penn Station with a switchover in Ronkonkoma. On the North Fork, there are train stops in Riverhead, Mattituck, and Southold. There are also bus routes from Manhattan with the Hampton Jitney and their luxury line, the Hampton Ambassador

Traveling from Connecticut? The Cross Sound Ferry travels between New London and Orient Point and offers a full, daily timetable schedule. 

The hamlet of Mattituck has a small, privately owned airport that is available for public use. 

Places to Go

The town of Southold on the North Fork has several notable places of interest for individuals and families of all ages. For those who wish to discover more about local history and culture, visit such sites and attractions as Horton Point Lighthouse Nautical Museum, Southold Indian Museum, the Railroad Museum of Long Island in Greenport, and the East End Seaport Museum that is also in Greenport. 

There are dozens of wineries that stretch across the town of Southold. A selection of wineries to discover in Southold are Sparkling Pointe, One Woman Wines & Vineyards, Corey Creek Tap Room, Osprey’s Dominion in Peconic, Kontokosta Winery in Greenport, Sannino Vineyards, and Pugliese Vineyard in Cutchogue. 

Southold is also home to such breweries as Greenport Harbor Brewing Company in Greenport and Eastern Front Brewing Co. in Mattituck. 

The majority of the breweries and wineries in Southold are open year-round as well as seven days a week. 

Specifically for families with young children, places in the town of Southold to visit include Cedar Beach County Park (a public beach), Lavender by the Bay in the hamlet of East Marion, the Antique Carousel in Village of Greenport, North Fork Flower Farm, and Laurel Lake Preserve.      

Where to Dine

Southold on the North Fork has an abundance of casual and fine dining establishments. Many of these restaurants are family owned and operated, and have been in business for decades. Visitors can easily discover the true character and charm of the North Fork by visiting the many locally owned restaurants. We divided recommended restaurants by hamlet:


Touch of Venice for Italian fare in a relaxed dining experience. Outdoor dining is available. 

Braun Seafood Co. for seafood chowder and plenty more seafood favorites, beloved by locals. 

Red Roaster Bistro for homestyle American meals with old-fashioned, rooster-themed decor. 

East Marion

Hellenic Snack Bar and Restaurant for Greek comfort classics. Ample outdoor dining is available. 

Angel’s Country Store for quick sandwiches, salads, and snacks. 


Cliff’s Elbow Room Too! for burgers, steaks, and seafood dishes in a local tavern. 

Hallock’s Cider Mill for homemade pies, local, produce, soups, and more. 


Love Lane Kitchen for a wide range of comfort food selections with house roasted coffee. Outdoor dining is available. 

A Mano for wood-fired pizzas, pastas, and Tuscan-style steaks.  

East On Main for burgers, steaks, pastas, and more tavern style fare. 

New Suffolk

Legends for upscale American fare and a casual sports bar that features over 200 types of beer. 

Case’s Place for a wide range of seafood fare as well as burgers and salads. Waterfront dining. 


The Frisky Oyster for American bistro fare for local ingredients and a fun, hipster vibe. 

PORT Waterfront Bar & Grill for an array of fresh seafood and pub fare, located on the waterfront. 

Noah’s for New American fare with a menu that features small plates with a strong emphasis on local ingredients. 


Duryea’s Orient Point on the waterfront features a selection of seafood including their famous Lobster Cobb salad.


Wednesday’s Table for sandwiches, soup, and coffee.

A Lure Chowder House features locally sourced seafood with local wine. There is a fireplace inside. 

North Fork Table & Inn for upscale farm and sea cuisine with a strong wine and cocktail list. 

Erik’s Breakfast & Lunch is a daytime cafe that offers a selection of egg sandwiches, seafood, burgers, and more. 

Annual Activities in Southold

Southold is known for hosting a wide selection of annual events that are perfect for everyone to enjoy. One of the most popular events is the Maritime Festival in Greenport that typically takes place during the last weekend in September. For 2023, the Maritime Festival is scheduled for Saturday, September 23rd and Sunday, September 24th. 

Southold hosts several holiday fairs during the months of November and December. 

One of the most famous events is at the beginning of the summer season: the Mattituck Strawberry Festival – For 2023, June 14th -18th.

Lodging in Southold

The town of Southold on the North Fork has a wide variety of hotel accommodations and lodging options. 

Sannino Vineyard Bed & Breakfast located in Cutchogue, in the heart of Long Island’s Wine Country, is a romantic North Fork getaway. Choose from a Tuscan styled Suite or Villa, both with stunning views of the main estate and sustainable vineyards. Luxurious amenities, a Chef’s Choice full hot breakfast delievered to you each morning and a complimentary tasting and cheese platter for two at the Tasting House is included with your stay.

Sound View Greenport is an iconic waterfront property where every guestroom has a waterview. This hotel is well known for their attention to detail, and high end amenities. Sound View also has an onsite restaurant called Halyard. 

Shorecrest Bed and Breakfast is set near a private beach close to the Old Field Vineyards and Sparkling Pointe winery. Amenities include breakfast, laundry, airport shuttle service, and bicycle rentals. 

The Shoals Suites & Slips is a tranquil hotel that features 20 suites and 20 slips on Peconic Bay. Modern comforts and amenities include robes and slippers, mood lighting, kitchenette, bath products by Malin + Goetz, wireless internet, and much more. The Shoals also offers waterfront yoga classes taught by The Giving Room. 

The Harborfront Inn is a charming property located within walking distance to many shops, restaurants, and ferry to Shelter Island in the village of Greenport. The hotel features traditionally decorated rooms and suites. Free breakfast is offered and there is an outdoor pool. 

Cedar House on Sound Bed and Breakfast in Mattituck is set within a converted barn on the grounds of a vineyard. The B&B features a variety of contemporary rooms and suites. Overnight stays include a two-course breakfast served in their open-plan kitchen and dining room. The common area or great room includes such amenities as a large flatscreen TV, 24-hour self serve coffee and tea station, game table, billiard table, and more.